반응 #955950

반응 방정식

trimethylsilyl-acetylene

3

5,5′-dibromo-2,2′-bipyridine

→

4

5,5′-Bis((trimethylsilyl)ethynyl)-2,2′-bipyridine

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGIt was stirred together with activated carbon for 20 minutes
2. 2
   여과filtered over celite
3. 3
   기타Then the solvent was removed under reduced pressure
4. 4
   기타sonicated for 15 minutes
5. 5
   여과filtered over celite
6. 6
   기타again yielding an orange solution
7. 7
   기타The solvent was removed under reduced pressure
8. 8
   기타the residue was purified by flash column chromatography on silica (eluent: CH2Cl2)

실험 절차

Under dry nitrogen atmosphere, successively trimethylsilyl-acetylene (619 mg, 6.30 mmol), [Pd(PPh3)2Cl2] (112 mg, 159 μmol), CuI (54.5 mg, 286 μmol) and DIPA (4 ml) were added to a stirred suspension of 3 (500 mg, 1.59 mmol) in 30 ml THF. While the mixture was stirred for 24 hours at room temperature, its color turned black. It was stirred together with activated carbon for 20 minutes and filtered over celite. Then the solvent was removed under reduced pressure, the residue was resuspended in hexane, sonicated for 15 minutes and filtered over celite again yielding an orange solution. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica (eluent: CH2Cl2) to yield 430 mg (1.23 mmol, 78%) of pure 4 as an off-white solid. 1H NMR (CDCl3, 250 MHz): δ=8.71 (s, 2H, bpy-H), 8.33 (d, 2H, JHH=8.3 Hz, bpy-H), 7.85 (d, 2H, JHH=7.8 Hz, bpy-H), 0.27 (s, 18H, Si(CH3)3).

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